What are the Best Boots to Wear for Date Night? | Lands' End

What are the Best Boots to Wear for Date Night?

When it comes to choosing an outfit for date night, the right pair of boots can take your look to the next level. One of the best things about this type of footwear is its versatility. There are boots that look great with women’s dresses, jeans, leggings, and jeggings. Boots can be worn in every season — there are fall and winter boots and those appropriate for spring and summer. No matter what is your date-night style, it’s easy to find a pair of boots for the occasion. Read on to learn more about different boot styles and how to wear them.

The Ankle Boot

Ankle boots come in lots of different styles and colors to coordinate with your wardrobe. You could go for a pair of black or brown side-zip ankle boots with a low heel if you’re looking for versatility. This boot style can be worn with a maxi skirt or jeans — especially skinny jeans or boot-cut jeans. You can even wear ankle boots with leggings. For a classic monochromatic look, pair black boots with black leggings. If you’re the trendy type, wear brown boots with black leggings for a photo-worthy look.

Coordinating your top and handbag with your ankle boots is another way to create a polished look for your next evening out. For example, if you opt for leopard-print ankle boots, wear a brown or black top and add a leopard-print bag. Classic black boots go with any color of women’s sweaters and can be matched to a black handbag. You can also play with different color combinations for a bold look — for example, black boots and a red handbag.

The Mid-Calf Boot

Another option is the mid-calf boot. This boot style falls in between the ankle and riding boot when it comes to length. There are mid-calf boots that slip on and those with zippers. Like ankle boots, they come in various colors and textures. You’ll find leather and faux leather mid-calf boots, as well as those with a velvety suede finish (which can also be faux!).

Mid-calf boots are elegant with a maxi skirt, but you can also wear them with a midi skirt. They also look stylish with jeans. You can wear them with straight-leg jeans or go for an on-trend look by pairing them with high-rise jeans. As with every boot style, mid-calf boots also go well with skinny jeans, leggings, and jeggings. Wear a pair of mid-calf boots with black jeggings and a women’s tunic sweater for an outfit that’s comfortable and polished.

The Riding Boot

Look and feel your confident best on a date night in a pair of equestrian-inspired riding boots. These boots come in rich leather and faux leather, in colors like saddle brown and black. Slip them on over your favorite leggings or jeans. You can wear them with any length skirt, including the mini. There are slip-on riding boots and those that zip, so it’s easy to find a pair that’s comfortable and suits your personal style.

Riding boots look classic with button-up blouses, but you can also wear them with roomy sweaters or even flowing tunic tops. These boots are a great date-night option for when you want a dressy look that’s not too formal. Riding boots and other tall boot styles often have a flat heel, but you can also find riding boots with a one- or two-inch heel if you want a little height. The riding boot has a classic look that can be dressed up or down depending on the accessories you choose. For a preppy look, finish your outfit with pearls. If you like a casual style, consider wearing silver turquoise jewelry.

Rain Boots and Snow Boots

Dance in the rain in a pair of durable duck boots. These boots are waterproof, so you can make the most of those rainy-day dates. Some duck boots are insulated for warmth, making them great for winter wear. And speaking of winter, there’s no need to cancel your date if it snows. Just wear a pair of snow boots to protect your feet against the elements. If you’re going on a dressy date, carry a pair of heels or flats in your bag and change when you get to your destination. For a casual date, you can wear your snow boots the entire time, as many styles are relatively lightweight and look great with jeans or leggings.

Boots aren’t just great for date night — they’re also good for everyday wear. There are so many timeless and on-trend boots from which to choose that you’ll want a pair of each. Don’t worry about fashion rules when buying boots; instead, choose what looks and feels best to you. A good pair of boots is an investment in your wardrobe that can serve you for years to come.


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